Jack Pasquella is perhaps the most trendy boy who graces the halls of the already fashionable Lake Forest High School. You’ll see him sporting Supreme, Adidas, and APC every day, and more importantly, he’ll be sporting them proudly.

From his round framed glasses to his undercut hairstyle, Pasquella clearly doesn’t stick to the standard and stereotypical LFHS male wardrobe–khakis, a Vineyard Vines pullover, and sneakers (assorted brands)–but that’s just how he likes it.

Jack hasn’t always considered himself the fashionable type and was certainly not always as progressive as he is today. He grew up attending St. Mary’s School in Lake Forest, where uniforms are mandatory. So Jack paid his due diligence, complete with the navy pants, generic white polo, and a navy (or yellow if you’re really bold) pullover with oh-so-awkwardly-short sleeves. However, when he hit high school, he became the trendsetter he is today. Freshman year, he was particularly into his footwear and sophomore year he began to expand his interests and additional attention into clothes.

And he isn’t just “into” clothes; he knows his stuff about designers, too. Though you may know them for their music, two men he admires the style of are Kanye West and A$AP Rocky. Both rappers have a genuinely unique fashion sense, which was brand new information to me. Pasquella says what sets the musicians apart from other fashion icons is the notion that, “almost everything they wear, he likes–and they wear brands he [Pasquella] has never heard of before.” Another icon of Jack’s is Hedi Slimane, an experienced designer who first designed for Dior and now for Yves Saint Laurent. In Jack’s own words, he is “very iconic.”

Now you may wonder where Jack buys all of his trendy apparel on the budget of a high school junior. The answer? Grailed.com. Grailed is a resale site that is strictly dedicated to high-end men’s clothing. And how he affords it all? Well, according to Jack, not everything he buys and sports has to be expensive. Rather, you have to be a creatively smart shopper.

“There are ways to getting around the pricey-ness of clothes,” Jack explained to me. “I don’t buy expensive pants, I just get all my pants tailored. All my jeans are pretty cheap but just tailored to fit me, and I’ll rip them myself if I want to.”

Jack may already own some of the items he likes, but he has a long list of potential future purchases, including a Saint Laurent shearling overcoat, Bottega Veneta chelsea boots or the Rick Owens’ mainline dunks from 2008. “The coat is just, like, you’re a baller if you wear that coat.” Pasquella shares with a wry smile. “The boots are very high-end Chelsea style boots, and the dunks are my favorite Rick Owens’ design.”

As any trendsetter has experienced, Jack deals with his fair share of detractors. The kids walking down the halls who are comfortable in their sweatpants and t-shirt without any sort of conscious thought, or those who think that style is purely a woman’s game might snark, “Dude, what are you wearing?”

But Jack knows exactly how to respond. “Kids used to, like, rip on me I guess but no one really rips on me anymore because if you’re wearing a fifteen dollar K-Mart outfit that your mom got you to begin with, I am going to obliterate you–like, really? Where is the premise of their argument?” Enough said, I suppose.

Pasquella will continue to be the trendiest Lake Forest High School boy by putting the time and effort into fashion that most men don’t (or find themselves too laid back to admit to). But Jack is a laid back guy as well. He’s a smart (multiple AP classes), athletic (Varsity Tennis), and down-to-earth guy. He knows how to get around price barriers to complete the look he wants, but still has his eyes on designer items.

You can always look to him for the coolest apparel and while you’re at it, boys, take notes. A sense of style never hurts.